UCL Magazine - Di Maria, Zubimendi and Buruk interviewsSep 29
It's set to be a huge clash and a season-defining one for both teams but who will come out on top? Here's three reasons to watch the conclusion to one of the standout ties of the last 16, live on BT Sport 1.
Antonio Conte out for revenge against the old enemy
It was an unhappy return to the San Siro for Antonio Conte three weeks ago as the former Inter boss left with a disappointing 1-0 first-leg defeat.
Conte won the league in charge of Milan's city rivals and would relish the chance to turn things around and knock out the Rossoneri in north London.
Never one to shrink when the limelight is on, should the tie reach boiling point then viewers can guarantee the ex-Italy and Juventus boss will have his say.
Conte faced another of his former clubs last weekend when his Tottenham side defeated Chelsea 2-0 and Spurs fans will hope he's in the mood to do more of the same come Wednesday night.
The 53-year-old suggested a return to Italy was in his long-term future after the defeat to Milan at the San Siro, saying: “I don’t want to talk about the future but as a former Italian national manager people know how much Italy means to me.
“It’s in my heart. I will never exclude the possible idea that I will be back here one day.”
For now, Spurs fans will hope Conte is content on knocking out Italian opposition.
Milan looking to revive their role as European heavyweights
With seven European Cup wins, only Real Madrid have claimed Europe's top prize more times than Italian giants AC Milan.
Milan have not lifted the Champions League since 2007 when they won a rematch against Liverpool and have not made it past the quarter-final of the competition since 2012.
After claiming the Serie A league title last season, Stefano Pioli's side are way off the blistering pace set by Napoli this term.
Which means Milan would do well to focus on progressing in European competition and with a 1-0 lead to carry over from the first leg, supporters will be hoping it's a step on the way back to former European glories.
Secure a result at the Tottenham Hotspur Stadium and former European kings Milan will be in the last eight for the first time in 11 years.
Who will come out on top in the battle of the forwards?
In an era where many teams are playing without No 9s, Tottenham's meeting with AC Milan will see a number of traditional forwards on display in London.
Tottenham will once again turn to talisman Harry Kane to do the business and dig them out of their deficit they find themselves in from the first leg.
The England skipper failed to hit the target at the San Siro but Antonio Conte will be hoping his main man - who will be supported by two of Richarlison, Son Heung-min and Dejan Kulusevski - can make amends on home turf.
Stefano Pioli will have a big call on his hands over who to start for the second leg with ex-Arsenal forward Olivier Giroud chosen to lead the line in recent weeks.
But returning veteran Zlatan Ibrahimovic is back in the fold while Rafael Leao - often used on the left - and even ex-Liverpool man Divock Origi could be pushing for a selection.
Whoever Pioli names in his starting XI will have a big impact on whether Milan make it through to the quarter-finals.